Step 1: Cut Your Pineapple In Quarters

For this you will need at least one pineapple, a cutting board, and a knife. I prefer using a long, sharp knife that isn't too wide (not as wide as a chef's knife, but bigger than a filet knife). Sometimes they're called a kitchen knife or a utility knife. Most importantly, use a knife you are comfortable with.
First cut your pineapple in half lengthwise.
Then cut each half in half, also lengthwise.
Now your pineapple should be cut into four pieces.

Step 2: Separate Core From Pineapple

Starting at one end of the pineapple, cut through the pineapple just beneath the core, working your way the full length of the pineapple.
The closer to the core the knife is, the more pineapple there will be to eat. The knife should come through the pineapple to the other side as seen in the photos. Your knife blade should be parallel to the cutting board/counter top.
It is very important that you don't fully remove the core from the pineapple. It should still be attached at each end.

Step 3: Cut The Skin Away From The Pineapple

This step is done twice, once on each side of the pineapple.
Starting at the top of the pineapple where the core cut begins, cut the pineapple away from the skin. You should be as close to the skin as you can without poking through the skin. This will maximize the edible part of the pineapple. The more stopping and starting you do the funkier your boat will look, so try to cut in one fluid motion.
Now repeat this on the other side.
When you are done the edible part of the pineapple should be completely detached from the core and the skin, but still sitting in place. Try poking and wiggling at the pineapple to see if this is true. If its still attached somewhere, find out where and cut it loose.